-by erin94 on ao3
Troye was running late. He was supposed to be at the sorority house five minutes ago, but yet he's running to the library with the book he forgot to return the day before. He knows this will just ruin his chances with the one sorority willing to let him in. Tonight is his informal rushing and he is supposed to attend the Phi Beta Sigma fraternity's party with the girls to prove his worth. They were already skeptical of letting a boy join, but Troye has always been incredibly feminine and enjoyed acting and being treated like a girl. His facial features and small body led to the image, not to mention the way he dressed. While he didn't (usually) go around wearing women's clothes (in public) he did often wear things other guys saw as inappropriate. He loved pink, skin tight, and sparkly things, not to mention his love for lace (especially lace panties). The girls were comforted by the fact that he was gay and wouldn't try hitting on them, but were still hesitant. Troye' worry about the upcoming party and his acceptance clouded his mind as he ran through the library doors and straight into a tall muscular chest. Troye bounced back from the boy, hit the doors and finally fell to his knees dropping his book and his glasses along the way.
"Are you alright?" came a concerned voice from above him.
The boy leaned down and picked up Troye' glasses before sliding them onto his face. With the boy now in focus, Troye could tell he ran into what could only be a god. He had curly brown hair partially hidden by a backwards snapback, shiny green eyes, and dimples too. It was like his ultimate dream boy (and masturbation fantasy) come to life. The boy stood back up allowing Troye a great chance to check out his (amazing) body.
"Yeah I'm fine" Troye stuttered out in complete awe.
"Are you sure? You might need a band-aide I think you scraped your knees falling for me" the boy winked and offered Troye a hand to help him up. Troye scoffed and rolled his eyes at the terrible line. The boy brought him closer to his chest again and whispered in his ear, "It's alright it wont be the last time you're on your knees for me." Then the boy walked off leaving Troye to collect his fallen book and will his erection away.
*
Almost all of the girls were finished getting ready by the time Troye made it to the Delta Zeta house. Troye walked in to the main bathroom to see the sorority president, Megan, smirking in his direction.
"Oh Troye it's nice of you to finally join us." Megan said in a sickly sweet tone.
"Yeah sorry... I was caught up at the library." Troye apologized glancing around at all the girls fixing themselves in front of the mirrors.
"Oh it's alright, you'll just have to do something a little... extra to get back in our good graces." Megan's smirk turned into an evil grin.
"And what is that?" Troye asked, a little uneasily.
"Well first of all, you need to let us give you a make over before we leave..."
"I can do that" Troye rushed to agree, he could deal with looking like an idiot at a party if it meant getting into the sorority.
"Well that's not all. You have one more thing you need to do, and this time you have two options." Megan's grin spread a little wider increasing Troye' unease.
"You can either hook up with Phi Beta Sigma's President Jacob Bixenman," the girls in the room with them laughed "or steal his prized honor's trophy out of his room... without being caught." Megan finished with her evil grin and a look that said she knew Troye wouldn't be able to do it. Despite Megan's lack of confidence, Troye gave a nod of understanding and Megan left the room.
Troye turned to the girls who would be giving him his makeover and asked, "What's so funny about sleeping with Jacob Bixenman?"
"He's never once slept with a sorority girl, so good luck." The girl smirked while forcing him down into a chair in front of the mirror.
*
That's how Troye found himself entering the frat house in a short tight skirt, a low hanging tank top with the sorority letters (DZ) on the front, and in full make up. It wasn't as bad as he was expecting and it's not like he minded much anyway, he enjoyed the looks the boys gave him as he and the sorority girls made their way to the kitchen for drinks. For a second, Troye thought he saw Library Boy in the corner but he assumed it was a trick of the low lighting and crowded room.
After taking a few shots, their group dispersed. Many of the girls went to dance and Troye followed them. After a few hours of drinking and dancing, the girls had either gone home with someone already or were ready to head back to their house. Troye knew it was now or never for stealing the prized trophy and winning the hearts of his sorority. He hadn't seen any sign of this mysterious President and had quickly given up on the idea of seducing him. With the directions of his fairly inebriated sorority sister he headed up the stairs and down the hall in search of the boy's room. It really helped that they had their names written on white boards on the door, allowing Troye to find the room in seconds. With an easy shove the door opened to a dark empty room. Troye flipped on the light and shut the door behind him. It wasn't hard to find the trophy seeing as it was on a shelf mounted to the wall surrounded by hanging fraternity paddles. As Troye stepped closer he could see all of the paddles had the fraternity letters and most had Jacob's name on them. There was one more decorated than the others, with Jacob's name in wooden letters sticking out from the paddle. It was a little odd, seeing as the letters were on in reverse. Troye softly ran his fingers over the name before a loud bang from the hallway behind him made him focus on why he was there. He grabbed the trophy before spinning around and stopping in his tracks. The Library Boy was standing in the door way, only this time he was dressed in skinny jeans, a tank top (showing off some drool worthy muscles and tattoos), and a backwards snapback with his curls peaking out underneath. The boy glanced over Troye body and down at the trophy Troye still held in his hands.
"What are you doing with my trophy, DZ?" The boy, or Jacob, crossed his arms and leaned against the door frame.
"I... uhm... well" Troye stuttered as he felt a blush rise on his cheeks.
"Cause it seems like you were going to take it." Jacob smirked as he stalked across the room to where Troye was standing.
Troye only blushed more, staring at the ground and holding the trophy out for Jacob to take. Jacob took the trophy and reached his arm around Troye to put it back on the shelf. Troye grew dizzy from the heat of Jacob that close to him. Jacob put a hand on Troye waist before bringing his other under Troye' chin and raising his head to meet his eyes.
"You make a very pretty girl, DZ" Jacob grinned and glanced at Troye mouth.
"Thanks" Troye whispered as the blush continued to spread down his neck.
"I'm afraid I'm still going to have to punish you though." Jacob gently pulled Troye' hip until the fronts of their bodies were pressed together, and then bent his head and softly kissed Troye. It only lasted for a second, but left Troye in a daze.
Jacob reached around Troye and grabbed a paddle before leading Troye to the armchair near the side of the room with a hand on his waist. Jacob lifted the hem of Troye shirt before bringing it up and off of his body. Troye only got a glance at the paddle to recognize it as the one he had touched earlier, with Jacob's name sticking out slightly, as Jacob sat down. He was quickly bent over Jacob's lap and enjoyed the feeling of Jacob's hand rubbing his bum over the skirt.
"You're bum's fantastic" Jacob groaned and gave it a little squeeze before moving his hand to the seam. Troye could actually hear the moan fall from Jacob's mouth as he tugged the skirt down and off revealing the black lace panties stretched across Troye' ass.
"Fuck, you really are a pretty girl aren't you? Unfortunately pretty girls still get punished when they do something naughty don't they?" Jacob rasped his voice seeming to have gotten lower. Troye only whimpered at the feeling of his cock growing harder pressed against Jacob's leg.
"I asked you a question slut, you need to be punished don't you?" Jacob demanded in a rough tone with a quick smack of his hand to Troye' bum.
"Ah... Yes." Troye moaned.
"Yes who?" Jacob asked with another smack of his hand.
"Yes Daddy." Troye groaned at the sting Jacob's hands were leaving.
"Fuck." Jacob exclaimed and reached down to unbutton his pants.
"Are you ready for your punishment, little girl?" Jacob asked as he softly caressed the lace over Troye' bum once again.
"Of course Daddy." Troye whispered as he felt Jacob pull his panties down to his thighs.
"We won't take those fully off, I want to fuck you in them later." Jacob smirked as he massaged Troye' bare cheeks, dipping his fingers into the crease between the cheeks every once in a while to Troye' pleasure.
After a few minutes of being fondled, Troye was surprised when Jacob stopped touching him. He whined and wiggled a bit wanting those teasing touches to return.
"Shh baby, you need to keep still." Jacob murmured as he placed his hand in the middle of Troye' back to comfort him.
It was only a few seconds before Troye heard the wooshing of the paddle and felt the sting of it hitting his bum. Troye whined and wiggled more at the pain.
"Remember to keep still or you'll get more than I had planned." Jacob admonished while rubbing Troye' back.
Jacob brought the paddle down again, this time spanking Troye and not stopping. Troye had counted to five spanks before it started feeling good. His bum was almost numb considering Jacob kept striking it in the same place. By the time they reached ten Troye could barely stop himself from wiggling in pleasure. At fifteen Troye was gently rubbing his cocking against Jacob's thigh. By the time Jacob reached twenty spanks, Troye was whining and quickly humping his cock on Jacob's thigh. Jacob stopped at twenty-five, right before Troye orgasmed on Jacob's skinny jeans. Jacob ran his hands over Troye' red, hot bottom and gave a little laugh.
"You know the brothers gave me this paddle as a joke. Said I could brand whatever bitch I wanted with my name just from a simple spanking. I never thought I would use it, but damn my name sure looks good on your ass." Jacob smirked as Troye leaned up and glanced over his shoulder at his bum. Sure enough Jacob's name was red and almost bruised on his ass from where it stuck out from the paddle.
Troye gave a soft groan as Jacob bent down and gave a gentle kiss to each check before sliding his panties back up. Jacob gently slid Troye' legs to the ground and positioned him on his knees. With a smirk Jacob stood up and brought his pants and boxers down his thighs, just enough to get his cock out.
"I told you, you'd be on your knees for me again little girl. Now suck." Jacob demanded as he brought the head of his cock to swipe against Troye' lips. Troye brought Jacob's cock into his mouth and started suckling on the head. He went to grip the base with his hand before Jacob groaned and slapped it away.
"Keep your hands clasped behind your back." Jacob commanded as he slid further into Troye' warm wet mouth. Troye obeyed and clasped his hands behind his back as he sucked harder on the cock Jacob was feeding him. Before long Jacob threaded his hands through Troye' hair and shoved Troye' head down to meet his groin. Troye chocked a bit at having Jacob's sizable cock down his throat and Jacob moaned at the feeling of Troye' throat spasming around his cock. Once Troye relaxed his throat, Jacob started to gradually fuck his face faster and faster. Troye wanted to please Jacob so he tried his hardest to continue sucking as Jacob's cock slid in and out of his throat. Jacob was moaning louder and louder as he watched Troye take all of him. Before long Jacob was withdrawing his cock and laughing a bit as Troye tried to follow it with his mouth, clearly wanting more.
"Come on pretty girl let's get you on the bed." Jacob smiled and lifted Troye into his arms, being careful of his still sore ass. Troye was gently placed onto his stomach on Jacob's bed with his face in the pillows. Troye breathed deep enjoying the smell of Jacob and listened as Jacob rummaged around in his bedside drawer and removed his clothes. After a few seconds Troye could feel the bed dip from where Jacob had climbed on. Jacob grabbed another pillow, lifted Troye hips, and slid the pillow under making sure Troye' ass was spread and on display for him. Troye wanted to continue lying there and letting Jacob do all the work, but he couldn't help a quick glance back at the boy behind him. He saw what could only be described as a naked body carved by Michelangelo. Jacob's body was gorgeous and covered in even more tattoos. Troye wanted to trace them with his mouth, but those plans were foiled with the sound of the lube cap snapping open in Jacob's palm. Troye watched as Jacob slicked up three of his fingers before closing the bottle and tossing it to the side of the bed. With a grin Jacob moved the crotch of Troye' panties to the side and circled his hole with a finger. Troye gasped before moaning as Jacob slid his first finger into him. Jacob was surprised at how tight Troye was and his cock ached with the need to be inside. Troye was groaning from the feeling of Jacob's long finger inside of him, gently moving back and forth causing sparks of pleasure to shoot through Troye' abdomen. Jacob started moving his finger in and out faster once he noticed the look of pleasure on Troye' face. Once Troye started grinding back on the finger fucking him, Jacob added his second. A brief expression of discomfort crossed Troye face before he was back to thrusting against Jacob's hand.
"You really are a slut aren't you little girl? You're enjoying my fingers so much. I bet you can't wait for my dick. Imagine how good it'll feel inside you, how full you'll be." Jacob groaned as he watched Troye' ass cheeks bounce from the force of him thrusting back onto Jacob's hand.
"Oh yes, Daddy please... please fill me up." Troye moaned as Jacob finally hit his prostate with his fingers.
"You're being such a good girl for me sweetheart, you want my cock in you now?" Jacob asked as he stroked his dick at the sight of Troye being so desperate.
"Yes...Yes... Daddy." Troye whined even louder than his moans.
Jacob took his fingers out, ignoring Troye' little whimper at the loss, and spread Troye' legs even farther than what they had been. Jacob quickly lubed up his cock before pulling Troye' panties to the side and lining up. With one solid push, Jacob was sliding his cock into Troye' tight heat and Troye was moaning the loudest he had all night. Once Jacob was fully inside, he laid over Troye' back bracing one arm against the bed to take some weight off of Troye and brought the other hand to cover Troye' mouth. Jacob was so much bigger than Troye that he fully covered him on the bed; barely an inch of Troye skin was visible besides his legs that were spread out at an obscene angle.
Jacob brought his mouth to Troye' ear and whispered "Gotta be quiet baby don't want all the people at the party to hear do you? Hear how much of a slut you are, hear you moaning and begging for my cock?" With that Jacob started to thrust into Troye in a slow but hard rhythm. Jacob shifted his cock every few thrusts looking for that special spot in Troye that would really have him screaming. He could tell when he found it based on the way Troye suddenly clenched around his cock in the most delicious of ways and let out a loud moan despite Jacob's hand over his mouth. After that Jacob built up his pace, thrusting faster and faster into the boy beneath him. Troye could barely contain his sounds at this point, he was sure anyone in the hallways could hear him. Jacob covered his mouth harder, slightly tugging Troye' head back at an angle.
"You want everyone to hear you slut? By the sounds you're making you do. You want them to come up here and see what those noises are. See you getting fucked like the whore you are, wearing your lace panties with my name on your ass peaking out. Fuck. Maybe you even want them to join in. Put another dick in your mouth that'll keep you quiet." Jacob panted as he sped up his thrusts and watched Troye' hands grip the bead sheet. Troye knew he wouldn't last much longer with the way Jacob was hitting his prostate and his dick was grinding against the pillow under his hips.
"Fuck I'm so close. Being so good for me aren't you, such a good girl for me. Are you close? I want you to cum when I tell you, fuck I wanna cum up your ass, will you let me pretty girl?" Jacob grunted as his thrusts started to lose their rhythm. Troye nodded in response, to which question he wasn't sure but he figured both answers were a yes. He was so close to cumming against Jacob's pillow, but was fighting the urge. He wanted to be a good girl for Jacob.
"Fuck...Fuck...Fuck... Cum little girl, cum for me now." Jacob groaned as he thrusted hard into Troye' ass. Troye clenched around Jacob's cock as he released onto the bed below him, the feeling of his orgasm increased by the feel of Jacob spurting cum inside him and gently thrusting back and forth to ride his own orgasm out.
After a few seconds Jacob rolled off of Troye, both of them laid there panting for a while. Once Troye could feel the cum starting to cool from where it had dripped out of him, he figured it was time for him to go. He stood from the bed and released a groan of pain from the feeling in his bum. His legs almost felt like jelly and he couldn't imagine trying to walk all the way back to the sorority house. A few seconds after Troye' sound of pain, Jacob was in front of him ushering him back to the bed and guiding him down to lay on his stomach.
"It's okay just stay here for the night, yeah?" Jacob asked as he stroked Troye' hair in what he hoped was a comforting gesture.
"Okay" Troye mumbled already on the verge of sleep just from the feeling of Jacob's hand in his hair.
Jacob sighed and removed Troye' panties fully this time, before wandering to the bathroom to get a wet washcloth. By the time he got back Troye was letting out tiny snuffles of breath with his face smushed into one of Jacob's pillows. Jacob smiled down at the sleeping boy before quickly cleaning him of the sticky cum still left on his skin. After disposing of the washcloth, Jacob climbed into bed and threw an arm over Troye who shifted until he was spooned with his back against Jacob. Jacob smiled contentedly and quickly fell asleep.
*
Troye woke up in the morning with an incredibly sore ass. He shifted and groaned until he was lying on his stomach in the unsurprisingly empty bed. It wasn't like he was expecting Jacob to want to stick around. It was just... he had kind of hoped for more. Which was silly he knows considering exactly what had happened. But still he felt that no other boy had understood him as much as Jacob had. Troye was so caught up in his melancholy thoughts that he didn't notice the creak of the bedroom door as it opened. However, he did notice the smell of pancakes as it wafted through the room. He lifted his head and made eye contact with Jacob carrying what appeared to be breakfast for two on a tray with tea and everything. Jacob paused in his motions unsure how Troye was feeling about him this morning. He was aware that he might have gotten a little carried away the night before, but he was hoping for more than a one-night stand. The tension was broken with a loud grumble from Troye stomach. Jacob let out a loud laugh at the sound and the blush that spread across Troye' face. Troye dropped his head back onto the bed with an embarrassed groan.
Jacob moved onto the bed, carefully positioning the tray on the nightstand. He rubbed his hand down Troye' back before asking, "How are you feeling this morning?"
"Like I'll never be able to sit again" Troye complained as he peeked up at Jacob.
"I'm sorry, I brought some painkillers and breakfast for you if you want it." Jacob offered with a dazzling smile. How could Troye say no?
"I'd like that but I don't know how I'm going to eat it when I can't even sit." Troye pouted.
"I have an idea!" Jacob announced before gathering all of the pillows on his bed and stacking them in his lap. He reached down and gripped Troye' waist before picking him up and positioning him on the pillows in his lap. Troye sighed at the feeling, the large amount of pillows cushioned his bum just enough for him to be comfy.
"Thanks, this is comfortable" Troye smiled as he leaned his body back against Jacob's. Jacob smiled and kissed the side of Troye' head before wrapping an arm around his waist. With the other hand Jacob reached for the tray and settled it across their laps. They had a wonderful breakfast where Troye learned he loved Jacob's laugh, and Jacob learned he loved Troye' smile. They both got to know each other and agreed upon meeting at the library for a study date later that day. When the painkillers kicked in and Troye felt up to leaving, Jacob lent Troye one of his many Phi Beta Sigma shirts and a pair of loose shorts that wouldn't hug his bum uncomfortably. Jacob even offered to drive Troye back to the Delta Zeta house.
"Thanks for the ride. I'll see you later today?" Troye reaffirmed, he still couldn't quite believe this was really happening.
"No problem, I will meet you at the library Troye." Jacob smiled and Troye blinked for a second. He couldn't remember ever telling Jacob his name come to think of it.
"How'd you know my name Jacob?" Troye questioned.
"Oh Megan told me who you were and what you were going to try and do last night. I thought about just letting you take the trophy, but after seeing you in that skirt I couldn't resist." Jacob explained with a wink and a smile. Troye sat dumbfounded for a few seconds before Jacob leaned over and gave him a quick kiss. Troye returned it in kind before making his way out of the car and into the house. He went straight to Megan's bedroom intent on giving her a piece of his mind. Troye entered without knocking and unsurprisingly found her in bed with a random guy. Megan had woken with a start at the sound of her door banging open and was surprised to find Troye in her room with several girls peeking in the door with interest.
"Ugh what do you want? Coming to tell me you didn't succeed?" She groaned into her pillow.
"Well that's what you would expect isn't it since you told Jacob what I was trying to do at the beginning of the party?" Troye accused with a hand on his hip and his eyebrows raised.
"So what it's not like it matters, you lost and now you can't join the sorority." Megan smirked at him.
"Well think again, I won. I slept with Jacob Bixenman." Troye announced with a triumphant grin.
"Hah prove it." Megan sneered.
"I'm wearing his clothes." Troye pointed out.
"Not good enough. You're a boy, you could have gotten them anywhere." Megan accused.
"I have his number." Troye argued.
"Could have gotten it from anyone." Megan dismissed.
"Fine. This good enough for you?" Troye huffed before he turned around, bent over, and pulled his pants down displaying one word prominently bruised onto his ass.
JACOB